benzyl (2SR,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-O-isopropylidene trihydroxyhexanoate

Base Information

• Chemical Name: benzyl (2SR,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-O-isopropylidene trihydroxyhexanoate
• CAS No.: 110594-80-4
• Molecular Formula: C₂₆H₃₁NO₈
• Molecular Weight: 485.534
• Mol file: 110594-80-4.mol

Synonyms:

Chemical Property of benzyl (2SR,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-O-isopropylidene trihydroxyhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2SR,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-O-isopropylidene trihydroxyhexanoate

There total 7 articles about benzyl (2SR,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-O-isopropylidene trihydroxyhexanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

acetic anhydride (108-24-7) + benzyl (2SR,3RS,5S)-2-benzyloxycarbonylamino-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate (110594-76-8,110594-77-9,110594-78-0,110594-79-1) → benzyl (2SR,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-O-isopropylidene trihydroxyhexanoate (110594-80-4,110594-81-5,110594-82-6)

Guidance literature:

With pyridine; dmap; for 3h; Ambient temperature;

DOI:10.1139/v87-031

Reference yield: 94.0%

acetic anhydride (108-24-7) + benzyl (2RS,3RS,5S)-2-benzyloxycarbonylamino-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate (110594-76-8,110594-77-9,110594-78-0,110594-79-1) → benzyl (2RS,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-O-isopropylidene trihydroxyhexanoate (110594-80-4,110594-81-5,110594-82-6)

Guidance literature:

With pyridine; dmap; for 3h; Ambient temperature;

DOI:10.1139/v87-031

Reference yield:

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (32233-43-5) → benzyl (2SR,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-O-isopropylidene trihydroxyhexanoate (110594-80-4,110594-81-5,110594-82-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / pyridinium chlorochromate, molecular sieves 3 Angstroem / CH₂Cl₂ / 1 h

2: 50 percent / 2M NaOH / H₂O; ethanol / 4 h / Ambient temperature; pH 9.8

3: dimethylformamide; H₂O / Ambient temperature

4: 2.07 g / triethylamine / dimethylformamide / Ambient temperature

5: 94 percent / pyridine, 4-dimethylaminopyridine / 3 h / Ambient temperature

With pyridine; dmap; sodium hydroxide; 3 A molecular sieve; triethylamine; pyridinium chlorochromate; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1139/v87-031

upstream raw materials:

acetic anhydride

benzyl (2RS,3RS,5S)-2-benzyloxycarbonylamino-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate

benzyl (2SR,3RS,5S)-2-benzyloxycarbonylamino-5,6-O-isopropylidene-3,5,6-trihydroxyhexanoate

2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol

Downstream raw materials:

benzyl (2RS,3RS,5S)-3-O-acetyl-2-benzyloxycarbonylamino-5,6-dihydroxy trihydroxyhexanoate

(d,l)-erythro-3-O-acetyl-2-benzyloxycarbonylamino-3-hydroxyglutaric acid α-benzyl ester

(d,l)-erythro-2-amino-3-hydroxyglutaric acid α-benzyl ester

(d,l)-erythro-3-O-acetyl-2-benzyloxycarbonylamino-3-hydroxyglutaric acid α-benzyl ester